CA2960324A1 - Substituted n,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents - Google Patents
Substituted n,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents Download PDFInfo
- Publication number
- CA2960324A1 CA2960324A1 CA2960324A CA2960324A CA2960324A1 CA 2960324 A1 CA2960324 A1 CA 2960324A1 CA 2960324 A CA2960324 A CA 2960324A CA 2960324 A CA2960324 A CA 2960324A CA 2960324 A1 CA2960324 A1 CA 2960324A1
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- Canada
- Prior art keywords
- mmol
- mixture
- methyl
- compound
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002260 anti-inflammatory agent Substances 0.000 title description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 170
- 238000011282 treatment Methods 0.000 claims abstract description 57
- 230000002265 prevention Effects 0.000 claims abstract description 27
- 230000003176 fibrotic effect Effects 0.000 claims abstract description 22
- 239000003814 drug Substances 0.000 claims abstract description 19
- 230000006806 disease prevention Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 336
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 208000035475 disorder Diseases 0.000 claims description 59
- -1 pentafluorosulfanyl Chemical group 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 57
- 239000011737 fluorine Substances 0.000 claims description 55
- 229910052731 fluorine Inorganic materials 0.000 claims description 55
- 239000012453 solvate Substances 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 39
- 229910052801 chlorine Inorganic materials 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 36
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 30
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- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 239000005557 antagonist Substances 0.000 claims description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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- 208000023367 bronchiolitis obliterans with obstructive pulmonary disease Diseases 0.000 claims description 8
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
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- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
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- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
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- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229940127296 soluble guanylate cyclase stimulator Drugs 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 102220480121 H/ACA ribonucleoprotein complex subunit DKC1_R10A_mutation Human genes 0.000 claims 1
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- 208000027866 inflammatory disease Diseases 0.000 abstract description 7
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 125
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 108
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14184040.5 | 2014-09-09 | ||
| EP14184040 | 2014-09-09 | ||
| PCT/EP2015/070318 WO2016037954A1 (de) | 2014-09-09 | 2015-09-07 | Substituierte n,2-diarylchinolin-4-carboxamide und ihre anti-inflammatorische verwendung |
Publications (1)
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|---|---|
| CA2960324A1 true CA2960324A1 (en) | 2016-03-17 |
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| CA2960324A Abandoned CA2960324A1 (en) | 2014-09-09 | 2015-09-07 | Substituted n,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents |
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| EP (1) | EP3191452A1 (enExample) |
| JP (1) | JP6618530B2 (enExample) |
| CN (1) | CN107074773A (enExample) |
| CA (1) | CA2960324A1 (enExample) |
| WO (1) | WO2016037954A1 (enExample) |
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| US10189788B2 (en) * | 2014-09-09 | 2019-01-29 | Bayer Pharma Aktiengesellschaft | Substituted N,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents |
| EP3271334A1 (de) * | 2015-03-18 | 2018-01-24 | Bayer Pharma Aktiengesellschaft | Substituierte n-bicyclo-2-arylchinolin-4-carboxamide und ihre verwendung |
| TWI770157B (zh) * | 2017-04-10 | 2022-07-11 | 德商拜耳廠股份有限公司 | 經取代之n-芳基乙基-2-胺基喹啉-4-甲醯胺及其用途 |
| BR112019021136A2 (pt) | 2017-04-10 | 2020-07-21 | Bayer Aktiengesellschaft | n-ariletil-2-arilquinolina-4-carboxamidas substituídas e uso das mesmas |
| AU2021341508A1 (en) | 2020-09-10 | 2023-05-25 | Precirix N.V. | Antibody fragment against fap |
| WO2023203135A1 (en) | 2022-04-22 | 2023-10-26 | Precirix N.V. | Improved radiolabelled antibody |
| CN119584994A (zh) | 2022-05-02 | 2025-03-07 | 普雷西里克斯公司 | 预靶向 |
| TW202504604A (zh) | 2023-07-26 | 2025-02-01 | 荷蘭商菲林公司 | 小分子前列腺素ｆ受體拮抗劑 |
| WO2025189066A1 (en) * | 2024-03-08 | 2025-09-12 | Athira Pharma, Inc. | Modulators of g protein-coupled receptor 55 (gpr55) |
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| PL186665B1 (pl) | 1994-05-27 | 2004-02-27 | Smithkline Beecham Spa | Pochodne chinoliny jako antagoniści receptorów NKtachykininy, sposób ich wytwarzania, kompozycja farmaceutyczna zawierająca pochodne chinoliny oraz ich zastosowanie |
| IT1270615B (it) | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
| AR004735A1 (es) | 1995-11-24 | 1999-03-10 | Smithkline Beecham Spa | Quinoleina 4-amido sustituida, un procedimiento para su preparacion, una composicion farmaceutica que los contiene y el uso de los mismos para lapreparacion de un medicamento. |
| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| DE19943635A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
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| DE19943639A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Dicarbonsäurederivate mit neuartigen pharmazeutischen Eigenschaften |
| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| CN1660811A (zh) * | 2004-02-27 | 2005-08-31 | 中国科学院上海药物研究所 | 1，4－二取代苯类化合物及其制备方法和用途 |
| CA2599992A1 (en) * | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Acridine and quinoline dervatives as sirtuin modulators |
| JP2011520969A (ja) | 2008-05-19 | 2011-07-21 | シェーリング コーポレイション | 二環式ヘテロ環誘導体およびｇｐｒ１１９モジュレーターとしてのその使用 |
| BRPI1013392A2 (pt) | 2009-03-31 | 2016-03-29 | Renascience Co Ltd | inibidor do inibidor-1 do ativador do plasminogênio |
| JP2011042643A (ja) | 2009-07-24 | 2011-03-03 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| WO2011153553A2 (en) | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| MX2013000198A (es) | 2010-07-09 | 2013-01-28 | Bayer Ip Gmbh | Pirimidinadas y triazinas condensadas y su uso. |
| DE102010040233A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| DE102010043379A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung |
| US20140275224A1 (en) | 2010-11-05 | 2014-09-18 | Regents Of The University Of Minnesota | Cytosine deaminase modulators for enhancement of dna transfection |
| EP2844638A1 (en) | 2012-05-03 | 2015-03-11 | Takeda GmbH | Novel ep2 receptor agonists |
| TWI572597B (zh) * | 2012-06-29 | 2017-03-01 | 美國禮來大藥廠 | 二甲基－苯甲酸化合物 |
| US9663488B2 (en) | 2013-01-28 | 2017-05-30 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| PT3083554T (pt) | 2013-12-17 | 2019-06-11 | Lilly Co Eli | Compostos de ácido dimetilbenzóico |
| US10189788B2 (en) * | 2014-09-09 | 2019-01-29 | Bayer Pharma Aktiengesellschaft | Substituted N,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents |
-
2015
- 2015-09-07 US US15/509,600 patent/US10189788B2/en not_active Expired - Fee Related
- 2015-09-07 WO PCT/EP2015/070318 patent/WO2016037954A1/de not_active Ceased
- 2015-09-07 CA CA2960324A patent/CA2960324A1/en not_active Abandoned
- 2015-09-07 CN CN201580060830.6A patent/CN107074773A/zh active Pending
- 2015-09-07 JP JP2017513052A patent/JP6618530B2/ja not_active Expired - Fee Related
- 2015-09-07 EP EP15757299.1A patent/EP3191452A1/de not_active Withdrawn
-
2018
- 2018-09-07 US US16/125,645 patent/US10479765B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP6618530B2 (ja) | 2019-12-11 |
| JP2017526701A (ja) | 2017-09-14 |
| US20170260140A1 (en) | 2017-09-14 |
| EP3191452A1 (de) | 2017-07-19 |
| US10479765B2 (en) | 2019-11-19 |
| US20190002409A1 (en) | 2019-01-03 |
| US10189788B2 (en) | 2019-01-29 |
| CN107074773A (zh) | 2017-08-18 |
| WO2016037954A1 (de) | 2016-03-17 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
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| FZDE | Discontinued |
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